US991735A - Octenediones. - Google Patents

Description

GEORG- MERLING- AND HUGO KOHLER, OF ELBERFELCD, GERMANY, ASSIGNORS T0 FARBENFABRIKEN VORM. FRIEDR. BAYER & (30., 0F ELBERFELD, GERMANY, A

CORPORATION 01 GERMANY.

OCTENEDIONES.

No Drawing.

To all whom it may concern:

Be it known that we, Gnonc MERLING, professor of chemistry, doctor of philosophy, and HUGO KoHLER, doctor of philosophy, citizens of the German Empire, residing at Elberfeld, Germany, have invented new and useful Improvements in Octene diones, of which the following is a specification.

The present invention relates to the man ufacture and production of the hitherto unknown octenediones which are derivatives of the 1.5-diketones of the formula:

These 1.5-octenediones are distinguished from the 1.3-octened1ones of the formula:

by the formation of normal oxims withhydroxylamin, with which the 1.3-diketones form iso-azoles. These substances show the further difference that the 1.3-diketones form cyclic ketones on contact with cone. sulfuric acid, while the 1.5-diketones do not form such ketones. The process for their production consists in heating methylene ketones or allowing them to stand for some time or by treating octadionol or its homologues with dehydrating agents. 611 starting 6. g. from methyleneethylmethylketone the unsaturated 1.5-diketone (dimethyloctenedione) Hn CH(CH )COCH2 cnz-oo-o cna)=cm is obtained.

The new bodies are valuable intermediate compounds for producing pharmaceutical products or other technically valuable products. They are limpid oils soluble in ether, alcohol and benzene.

In order to illustrate the new process more fully the following examples are given, the parts being by weight:

Example 1: Methyleneethylmethylketone is distilled several times. An oil of a higher boiling point is thus obtained which consists for the most part of dimethyloctenedione. By fractional distillation in cacao dimethyloctenedione is obtained in the shape Specification of Letters Patent.

Patented May 9, 1911.

Application filed June 28, 1910. Serial No. 569,331.

of a colorless refracting oil soluble in water and possessing an odor llke pinene. Its formatlon probably takes place according to the following equation: oH2=moan-oo-oH3+oH3ooo oH3)= on on COCH OH2 CH2 a) 3 oH2 ooo oH3 =cH,

It boils at from 8385 C. under a pressure of 17 mm. Its semicarbazone melts at 183 It is a limpid oil easily soluble in water. Boiling point 7576 C. under a pressure of 21 mm. Its semicarbazone melts at 199 C.

W e claim 1. The herein described 1.5 octenediones obtainable from methylene-ketones, which compounds are limpid oils soluble in ether, alcohol and benzene forming normal oxims with hydroxylamin, substantially as described.

2. The herein described dimethyloctenedione obtainable from methyleneethylmethylketone, which product is a limpid oil soluble in water and boiling at 83-85 C. under a pressure of 17 min, its semicarbazone melting at 183 0., substantially as described.

In testimony whereof we have hereunto set our hands in the presence of two subscribing witnesses.

GEORG MERLING. [L. s.] HUGO KOHLER. [n s.] Witnesses WALTER VONNEGUT, ALFRED HENKEL.

Copies of this patent may be obtained for five cents each, by addressing the Washington, D. G.

It is hereby certified that in Letters Patent No. 991,735, granted May 9, 1911, upon the application of Georg Merling and Hugo Kohler, of Elberfeld, Germany,

for an improvement in Ootenediones, an error appears in the printed specification requiring correction as follows: Lines 60 and 80, that portion of, the formula reading GH CH should read 0117 011g; and that the said Letters Patent should be read with this correction therein that the same may conform to the record of the case in the Patent Oflice.

Signed and sealed this 25th day of July, A. D., 1911.

E. B. MOORE,

Commissioner of Patents.

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